CA2417427A1 - Acetamide derivatives and the use thereof as inhibitors of coagulation factors xa and viia - Google Patents
Acetamide derivatives and the use thereof as inhibitors of coagulation factors xa and viia Download PDFInfo
- Publication number
- CA2417427A1 CA2417427A1 CA002417427A CA2417427A CA2417427A1 CA 2417427 A1 CA2417427 A1 CA 2417427A1 CA 002417427 A CA002417427 A CA 002417427A CA 2417427 A CA2417427 A CA 2417427A CA 2417427 A1 CA2417427 A1 CA 2417427A1
- Authority
- CA
- Canada
- Prior art keywords
- monosubstituted
- acetamide
- phenyl
- coar
- het
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 6
- 108010039209 Blood Coagulation Factors Proteins 0.000 title abstract description 5
- 102000015081 Blood Coagulation Factors Human genes 0.000 title abstract description 5
- 239000003114 blood coagulation factor Substances 0.000 title abstract description 5
- 150000003869 acetamides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims abstract description 6
- 238000002399 angioplasty Methods 0.000 claims abstract description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 6
- 208000037803 restenosis Diseases 0.000 claims abstract description 6
- 206010061218 Inflammation Diseases 0.000 claims abstract description 5
- 206010027476 Metastases Diseases 0.000 claims abstract description 5
- 230000004054 inflammatory process Effects 0.000 claims abstract description 5
- -1 aromatic heterocyclic radical Chemical class 0.000 claims description 150
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 108010074860 Factor Xa Proteins 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 208000034564 Coronary ostial stenosis or atresia Diseases 0.000 claims description 14
- 241001442234 Cosa Species 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
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- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- AJTZFWXGFTZATC-UHFFFAOYSA-N n-[(3-carbamimidoylphenyl)methyl]-n-phenyl-2-[4-(2-sulfamoylphenyl)phenyl]acetamide Chemical compound NC(=N)C1=CC=CC(CN(C(=O)CC=2C=CC(=CC=2)C=2C(=CC=CC=2)S(N)(=O)=O)C=2C=CC=CC=2)=C1 AJTZFWXGFTZATC-UHFFFAOYSA-N 0.000 claims description 2
- OOUBUWUOBMPYNO-UHFFFAOYSA-N n-[(3-carbamimidoylphenyl)methyl]-n-propyl-2-[4-(2-sulfamoylphenyl)phenyl]acetamide Chemical compound C=1C=C(C=2C(=CC=CC=2)S(N)(=O)=O)C=CC=1CC(=O)N(CCC)CC1=CC=CC(C(N)=N)=C1 OOUBUWUOBMPYNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 108010054265 Factor VIIa Proteins 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- XTLMZZXSCBYJHZ-UHFFFAOYSA-N n-[(3-carbamimidoylphenyl)methyl]-2-[4-(2-methylsulfonylphenyl)phenyl]-n-propylacetamide Chemical compound C=1C=C(C=2C(=CC=CC=2)S(C)(=O)=O)C=CC=1CC(=O)N(CCC)CC1=CC=CC(C(N)=N)=C1 XTLMZZXSCBYJHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010008190 Cerebrovascular accident Diseases 0.000 abstract 1
- 208000006011 Stroke Diseases 0.000 abstract 1
- 208000021156 intermittent vascular claudication Diseases 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 324
- 238000006243 chemical reaction Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 16
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 238000010265 fast atom bombardment Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 235000019441 ethanol Nutrition 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 108090000190 Thrombin Proteins 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 229960004756 ethanol Drugs 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003146 anticoagulant agent Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
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- 229940127219 anticoagulant drug Drugs 0.000 description 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
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- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/08—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10037146A DE10037146A1 (de) | 2000-07-29 | 2000-07-29 | Acetamidderivate |
| DE10037146.9 | 2000-07-29 | ||
| PCT/EP2001/007594 WO2002010127A1 (de) | 2000-07-29 | 2001-07-03 | Acetamidderivate und ihre verwendung als inhibitoren des koagulationsfaktors xa und viia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2417427A1 true CA2417427A1 (en) | 2003-01-27 |
Family
ID=7650757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002417427A Abandoned CA2417427A1 (en) | 2000-07-29 | 2001-07-03 | Acetamide derivatives and the use thereof as inhibitors of coagulation factors xa and viia |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20030187037A1 (ko) |
| EP (1) | EP1309549A1 (ko) |
| JP (1) | JP2004505106A (ko) |
| KR (1) | KR20030029531A (ko) |
| CN (1) | CN1444561A (ko) |
| AR (1) | AR029999A1 (ko) |
| AU (1) | AU2001281941A1 (ko) |
| BR (1) | BR0112813A (ko) |
| CA (1) | CA2417427A1 (ko) |
| CZ (1) | CZ2003465A3 (ko) |
| DE (1) | DE10037146A1 (ko) |
| HU (1) | HUP0301502A2 (ko) |
| MX (1) | MXPA03000780A (ko) |
| NO (1) | NO20030431L (ko) |
| PL (1) | PL358756A1 (ko) |
| SK (1) | SK1972003A3 (ko) |
| WO (1) | WO2002010127A1 (ko) |
| ZA (1) | ZA200301633B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200410921A (en) * | 2002-11-25 | 2004-07-01 | Hoffmann La Roche | Mandelic acid derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19819548A1 (de) * | 1998-04-30 | 1999-11-04 | Merck Patent Gmbh | Biphenylderivate |
| JP2003500386A (ja) * | 1999-05-24 | 2003-01-07 | シーオーアール セラピューティクス インコーポレイテッド | Ｘａ因子阻害剤 |
| AU5158100A (en) * | 1999-05-24 | 2000-12-12 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| WO2001068605A1 (en) * | 2000-03-13 | 2001-09-20 | Pharmacia Corporation | Polycyclic aryl and heteroaryl substituted benzenes useful for selective inhibition of the coagulation cascade |
-
2000
- 2000-07-29 DE DE10037146A patent/DE10037146A1/de not_active Withdrawn
-
2001
- 2001-07-03 CN CN01813469A patent/CN1444561A/zh active Pending
- 2001-07-03 WO PCT/EP2001/007594 patent/WO2002010127A1/de not_active Application Discontinuation
- 2001-07-03 JP JP2002516259A patent/JP2004505106A/ja active Pending
- 2001-07-03 PL PL01358756A patent/PL358756A1/xx unknown
- 2001-07-03 MX MXPA03000780A patent/MXPA03000780A/es unknown
- 2001-07-03 HU HU0301502A patent/HUP0301502A2/hu unknown
- 2001-07-03 BR BR0112813-2A patent/BR0112813A/pt not_active Application Discontinuation
- 2001-07-03 EP EP01960449A patent/EP1309549A1/de not_active Withdrawn
- 2001-07-03 US US10/343,196 patent/US20030187037A1/en not_active Abandoned
- 2001-07-03 SK SK197-2003A patent/SK1972003A3/sk unknown
- 2001-07-03 KR KR1020027017990A patent/KR20030029531A/ko not_active Application Discontinuation
- 2001-07-03 CZ CZ2003465A patent/CZ2003465A3/cs unknown
- 2001-07-03 CA CA002417427A patent/CA2417427A1/en not_active Abandoned
- 2001-07-03 AU AU2001281941A patent/AU2001281941A1/en not_active Abandoned
- 2001-07-27 AR ARP010103584A patent/AR029999A1/es unknown
-
2003
- 2003-01-28 NO NO20030431A patent/NO20030431L/no not_active Application Discontinuation
- 2003-02-27 ZA ZA200301633A patent/ZA200301633B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ2003465A3 (cs) | 2003-05-14 |
| DE10037146A1 (de) | 2002-02-07 |
| NO20030431D0 (no) | 2003-01-28 |
| SK1972003A3 (en) | 2003-06-03 |
| CN1444561A (zh) | 2003-09-24 |
| US20030187037A1 (en) | 2003-10-02 |
| JP2004505106A (ja) | 2004-02-19 |
| WO2002010127A1 (de) | 2002-02-07 |
| NO20030431L (no) | 2003-01-28 |
| AR029999A1 (es) | 2003-07-23 |
| AU2001281941A1 (en) | 2002-02-13 |
| HUP0301502A2 (hu) | 2003-08-28 |
| PL358756A1 (en) | 2004-08-23 |
| BR0112813A (pt) | 2003-07-01 |
| EP1309549A1 (de) | 2003-05-14 |
| ZA200301633B (en) | 2004-06-22 |
| MXPA03000780A (es) | 2003-06-04 |
| KR20030029531A (ko) | 2003-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |